March Madness 2023: The biggest NCAA Tournament upsets so far

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As the name implies, March Madness always delivers some level of mayhem through the first two rounds and beyond.

But nobody could have predicted what we saw in the opening weekend of this year’s NCAA Tournament.

In just four days, we saw two No. 1 seeds go down – one to a No. 16 seed that made the tournament on a technicality and another that lost in the second round less than a year after winning it all.

How’s that for some unbridled chaos?

Here’s a look at the five biggest moneyline upsets from the first weekend of this year’s NCAA Tournament, with odds courtesy of BetMGM:

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Munden Jr. #1 of the Fairleigh Dickinson Knights dunksGetty Images

No. 16 Fairleigh Dickinson (+1600) over No. 1 Purdue

Fairleigh Dickinson’s shocking win over Purdue in the first round wasn’t just the biggest upset of this year’s tournament.

It’s the biggest upset in March Madness history.

The Knights were dealing as high as 25/1 at some shops and were priced as a 23.5-point underdog at BetMGM – easily the largest spread for any upset in NCAA Tournament history.

It’s even more shocking, considering that FDU was the smallest team in the country and somehow managed to corral 7-4 center Zach Edey to pull off the monumental upset.

The win was only the second by a No. 16 seed in March Madness history, following UMBC’s historic victory over No. 1 seed Virginia in 2018.

This one was even more shocking, as FDU was profiled as one of the worst teams in the country and didn’t even win its conference tournament.

No. 15 Princeton (+750) over No. 2 Arizona

This game will forever be overlooked because of the historic nature of FDU’s win, but Princeton still managed to pull off one of the biggest upsets we’ve ever seen.

The Tigers were 15.5-point underdogs against Arizona heading into the first round and were catching 14.5 points a few hours before tip-off – making this the 10th-biggest upset in the history of March Madness, per BetMGM.

It was just the 11th time that a No. 15 seed has beaten a No. 2 seed and marked the biggest upset victory by an Ivy league team since the tournament expanded to 64 teams in 1985.

No. 15 Princeton (+225) over No. 7 Missouri

As if one historic upset wasn’t enough, Princeton doubled down on Saturday with another stunner to become the only double-digit seed in this year’s Sweet 16.

The Tigers were technically 6.5-point underdogs against Missouri but looked like the better team from the opening tip, leading for nearly 38 of 40 minutes and using a 13-2 run to pull away for good in the second half.

The win also propelled Princeton to the Sweet 16 for the first time in school history, one of just two Ivy League schools (2010 Cornell) to reach that stage since the tournament expanded in ’85.

Furman Paladins celebrate their win against Virginia CavaliersGetty Images

No. 13 seed Furman (+185) over No. 4 Virginia

The first shocker of this year’s tournament came at the expense of Virginia, which added to its checkered tournament legacy with a last-second loss to Furman.

The Paladins trailed almost the entire game and were down by 12 points midway through the second half before hitting six of their final 11 attempts from deep – including the game-winner off a shocking Virginia turnover in the final seconds.

Not only was it Furman’s second-ever NCAA Tournament win, but it was also just the fifth win in the first round by a Southern Conference team in 38 tries and snapped a 26-year drought for SoCo teams seeded 11th or worse.

No. 11 Pittsburgh (+165) over No. 6 Iowa State

This one doesn’t have the same mid-major flavor as the other big upsets on this list, but Pittsburgh still proved oddsmakers wrong with its dominant win over Iowa State in the first round.

The Panthers barely outlasted Tuesday’s play-in game with Mississippi State, but they came out hot three days later against Iowa State – racing to a 22-2 lead in the first half before slowing down by halftime.

They eventually pulled away with another 10-0 run down the stretch to secure the fifth-biggest moneyline upset of the tournament thus far.